1: 95 percent / Ba(OH)2 / Pd(0) 2: 70 percent / 1.) LDA; 2.) 50percent aq. HOAc / 1.) THF, reflux, 2.5 h; 2.) reflux, 10 min 3: 81 percent / Et3N / CH2Cl2 / -78 °C 4: 69 percent / LiCl, (2-furyl)3P / Pd2(dba)3 / various solvent(s) / 5 h / Ambient temperature 5: 90 percent / BCl3 / CH2Cl2 / 0.17 h / 0 °C View Scheme

1: 81 percent / Et3N / CH2Cl2 / -78 °C 2: 69 percent / LiCl, (2-furyl)3P / Pd2(dba)3 / various solvent(s) / 5 h / Ambient temperature 3: 90 percent / BCl3 / CH2Cl2 / 0.17 h / 0 °C View Scheme

1: 70 percent / 1.) LDA; 2.) 50percent aq. HOAc / 1.) THF, reflux, 2.5 h; 2.) reflux, 10 min 2: 81 percent / Et3N / CH2Cl2 / -78 °C 3: 69 percent / LiCl, (2-furyl)3P / Pd2(dba)3 / various solvent(s) / 5 h / Ambient temperature 4: 90 percent / BCl3 / CH2Cl2 / 0.17 h / 0 °C View Scheme

1: 69 percent / LiCl, (2-furyl)3P / Pd2(dba)3 / various solvent(s) / 5 h / Ambient temperature 2: 90 percent / BCl3 / CH2Cl2 / 0.17 h / 0 °C View Scheme

1: 96 percent / sodium hydride (80percent oil) / tetrahydrofuran / 1.5 h / Heating 2: 1.) magnesium turnings, iodine; 2.) iodomethane / 1.) THF, reflux; 2.) THF, reflux, then r.t. 2 h 3: 100 percent / H2 / palladium-on-carbon / ethanol / Ambient temperature 4: 4.6 g / thionyl chloride / 8 h / Heating 5: CH2Cl2 / Ambient temperature 6: 81 percent / tetrahydrofuran / 15 h / Ambient temperature 7: 1.) hydriodic acid; 2.) hydriodic acid / 1.) glacial acetic acid, reflux, 2 h; 2.) acetic acid, reflux, 7 h 8: 1.) potassium carbonate; 2.) pyridine, dimethylaminopyridine / 1.) DMSO, acetone, r.t., 2 h 9: 75 percent / N-bromosuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating 10: 1.) sodium borohydride, diphenyl diselenide; 2.) 30percent H2O2 / 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C View Scheme

sodium tetrahydroborate; diphenyl diselenide; dihydrogen peroxide 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C; Yield given. Multistep reaction;

1: 75 percent / N-bromosuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating 2: 1.) sodium borohydride, diphenyl diselenide; 2.) 30percent H2O2 / 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C View Scheme

1: 95 percent / potassium carbonate / acetone / 20 h / Heating 2: 96 percent / sodium hydride (80percent oil) / tetrahydrofuran / 1.5 h / Heating 3: 1.) magnesium turnings, iodine; 2.) iodomethane / 1.) THF, reflux; 2.) THF, reflux, then r.t. 2 h 4: 100 percent / H2 / palladium-on-carbon / ethanol / Ambient temperature 5: 4.6 g / thionyl chloride / 8 h / Heating 6: CH2Cl2 / Ambient temperature 7: 81 percent / tetrahydrofuran / 15 h / Ambient temperature 8: 1.) hydriodic acid; 2.) hydriodic acid / 1.) glacial acetic acid, reflux, 2 h; 2.) acetic acid, reflux, 7 h 9: 1.) potassium carbonate; 2.) pyridine, dimethylaminopyridine / 1.) DMSO, acetone, r.t., 2 h 10: 75 percent / N-bromosuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating 11: 1.) sodium borohydride, diphenyl diselenide; 2.) 30percent H2O2 / 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C View Scheme

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14.25 h / |Inert atmosphere 2.1: zinc; pyridine / chloroform / 0.33 h / |Inert atmosphere; |Reflux 3.1: potassium carbonate / acetone / 16 h / |Inert atmosphere; |Reflux 4.1: potassium carbonate / methanol / 0 - 20 °C / |Inert atmosphere 5.1: triethylamine / acetonitrile / 2 h / 60 °C / |Inert atmosphere 6.1: piperidine / tetrahydrofuran / 4 h / 20 - 70 °C / |Inert atmosphere 7.1: piperidine / water; benzene / 1 h / |Inert atmosphere; |Dean-Stark; |Reflux 7.2: 48 h / |Inert atmosphere; |Reflux 8.1: potassium hydroxide / methanol / 2 h / |Inert atmosphere; |Reflux 8.2: pH 4 9.1: BH3*SMe2 / tetrahydrofuran / 5.08 h / 20 °C / |Inert atmosphere 10.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / |Inert atmosphere 11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / |Inert atmosphere; |Reflux 11.2: 15 h / 20 °C / |Inert atmosphere; |Reflux 12.1: boron trichloride / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1.1: copper(l) chloride; oxygen / acetonitrile / 2 h 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14.25 h / |Inert atmosphere 3.1: zinc; pyridine / chloroform / 0.33 h / |Inert atmosphere; |Reflux 4.1: potassium carbonate / acetone / 16 h / |Inert atmosphere; |Reflux 5.1: potassium carbonate / methanol / 0 - 20 °C / |Inert atmosphere 6.1: triethylamine / acetonitrile / 2 h / 60 °C / |Inert atmosphere 7.1: piperidine / tetrahydrofuran / 4 h / 20 - 70 °C / |Inert atmosphere 8.1: piperidine / water; benzene / 1 h / |Inert atmosphere; |Dean-Stark; |Reflux 8.2: 48 h / |Inert atmosphere; |Reflux 9.1: potassium hydroxide / methanol / 2 h / |Inert atmosphere; |Reflux 9.2: pH 4 10.1: BH3*SMe2 / tetrahydrofuran / 5.08 h / 20 °C / |Inert atmosphere 11.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / |Inert atmosphere 12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / |Inert atmosphere; |Reflux 12.2: 15 h / 20 °C / |Inert atmosphere; |Reflux 13.1: boron trichloride / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme